Permanent wave-fixing composition and process

ABSTRACT

Process of treating the hair comprising first permanently waving the hair with a thio reducing agent and thereafter applying to the hair an aqueous solution containing a neutralizing agent and a water-soluble diimide compound.

United States Patent Inventors Appl. No. Filed Patented AssigneePriority Gregoire Kalopissis Paris;

Jean-Louis Abegg, le Perreux, both of France Feb. 28, 1968 Dec. 21 1971Societe Anonyme Dite: LOreal Mar. 3, 1967 France PERMANENT WAVE-FIXINGCOMPOSITION AND PROCESS 5 Claims, No Drawings US. Cl 132/7, 424/71,424/72 A6lk 7/10 llnt. Cl

Primary ExaminerAlbert T. Meyers Assistant Examiner-Doris J. FunderburkAttorney--Holcombe, Wetherill & Brisebois ABSTRACT: Process of treatingthe hair comprising first permanently waving the hair with a thioreducing agent and thereafter applying to the hair an aqueous solutioncontaining a neutralizing agent and a water-soluble diimide compound.

PERMANENT WAVE-FIXING COMPOSITION AND PROCESS In conventional permanentwaving processes the first step is to apply-to the hair a suitablereducing agent to rupture the 8-8 bonds of the keratin in the hair,after which the desired shape is imparted to the hair. An oxidizingcomposition is then applied, which serves to reconstitute the broken S-Sbonds.

as n

This last step is commonly called the neutralizing or oxidizing" step.

This invention relates to a new neutralizing composition which has theremarkable property of effectively restoring to its original state hairwhich has been damaged by the first step in permanent waving, or bybleaching.

It is an object of the present invention to provide a new compositionfor fixing" or neutralizing" permanent waves, which is essentiallycharacterized by the fact that it comprises in combination at least oneoxidizing agent and at least one carbodiimide.

The oxidizing agents may be selected from the group consisting ofhydrogen peroxide, the bromates and iodates of alkaline metals, thealkaline perborates, urea peroxide, chlorates, and polythionates such assodium tetrathionate. The concentrations of those oxidizing agents arethose normally used to neutralize permanent waves.

The carbodiimides of the composition according to the invention arecompositions which respond to the general formula:

R and R may be identical or different, and represent lower aliphatic orcycloaliphatic alkyl radicals containing one to six carbon atoms,aromatic radicals such as phenyl and tolyl or aralkyl radicals such asbenzyl.

In a preferred embodiment of the invention the carbodiimides are solublein the composition.

In this preferred embodiment of the invention, the neutralizingcomposition is an aqueous solution containing at least one carbodiimideresponding to the formula:

in which:

R, has the significance indicated under formula l,

R and R are identical or different lower alkyls containing one to fourcarbon atoms such as CH or Cal l5. R, and R may also form part of aheterocyclic remainder, such as, for example, morpholine or piperidine,

n is a hole number between 2 and 6 inclusive.

In one particular embodiment of the composition according to theinvention, the tertiary amine function of the carbodiimide according toformula ll may be quaternized in a conventional manner by means of alower alkyl halide, such as methyl iodide, or by an alkyl sulfate orsulfonate, such as methyl sulfate or methyl paratoluene sulfonate.

Among the carbodiimides which may be used in the composition accordingto the invention are, for example:

the monocarbodiimides, such as:

[l-ethyl-3-(3'-trimethylammonium) propyl carbodiimide] iodide respondingto'the formula:

[l-cyclohexyl-3-(2'-methyl morpho linium) ethyl carbodiimide]paratoluene sulfonate responding to the formula:

[l-ethyl-3-(2'-methyl morpholinium) ethyl carbodiimide] paratoluenesulfonate responding to the formula:

[l-cyclohexyl-3-(2'-diethyl methylammonium) ethyl carbodiimide]paratoluene sulfonate responding to the forl -ethyl-3-( 3'-trimethylammonium)propyl carbodiimide] paratoluene sulfonateresponding to the formula:

and [l,l'bis (3"-trimethylammonium propyl) 3,3-hexamethylenedicarbodiimide] diiodide responding to the The above carbodiimides havebeen listed purely by way of example, and may be used singly or inmixtures containing two or more of them.

In accordance with the invention the concentration of carbodiimides inthe composition may range from bout 0.1 to 10 percent and preferablyfrom 2 to 6 percent.

The pH value of the composition according to the invention may varywithin broad limits, but it is in general determined by the nature ofthe oxidizing agents used for neutralization, and is preferably between4 and 8.

The composition according to the invention may also take the form of anemulsion, gel or cream, and may contain any of the additivesconventionally included in cosmetic compositions for used for carryingout the neutralizing step in permanent waving processes.

It is also an object of the present invention to provide a new method ofcarrying out this neutralization, which method is characterized by thefact that a composition having a carbodiimide base and oxidizingcompounds are applied to the hair and left in contact therewith for atleast 5 minutes and generally about 15 to 60 minutes, at a temperaturebetween 25 and 50 C., for example.

The concentration of the oxidizing compounds is, for instance, 5 to 20percent for compounds like potassium bromate or sodium bromate and l to5 percent in weight for hydrogen superoxide, the concentration of thecarbodiimide being between 0.1 and percent. 7

Thus when the hair has first been bleached, the composition according tothe invention is applied in exactly the same way as those used in theconventional neutralization of a permanent wave, that is to say, forabout minutes, at the ambient temperature.

On the other hand, when hair which has not been bleached is neutralized,neutralization with the product according to the invention is fullyefficacious only at higher temperature, for example, of the order of 50C. and when applied for a longer time, of the order of minutes, forexample.

The neutralizing process according to the invention makes it possible tosubstantially improve the cosmetic properties of hair treated therewith,which presents a more attractive appearance, is softer to the touch,fluffier, and takes subsequent sets better than hair which has not beentreated in accordance with the invention.

It should moreover be noted that treatment with the compositionsaccording to the invention makes it possible to obtain a reduction ofabout 30 to 40 percent in alkaline solubility of the hair at the end ofthe permanent in the case of bleached hair which has been treated inaccordance with the invention, as compared with hair waved in aconventional manner.

lt will be recalled that the tenn alkaline solubility" is defined as therelative decrease in the weight of hair treated with N/ 10 sodiumhydroxide under the conditions specified in the international standardsset forth in the l.W.T.O. report.

In order that the invention may be better understood, several exampleswill now be described, purely by way of illus' tration, withoutsuggesting that the scope of the invention is limited to the detailsthereof.

EXAMPLE I Hair which has first been bleached with a conventionaloxidizing agent is permanently waved in a conventional manner, using a 4percent solution of ammonium thioglycollate, the pH value of which hasbeen adjusted to 8.2 with ammonia or a suitable buffering agent. Aftercompletion of the first permanent waving step in a conventional manner,the following solution is applied to the hair:

Sodium bromate 5 g. l-cyclohexyl-3-(2'-methylmorpholinium) ethylcarbodiimide] paratoluene lulfonate 2 g. Water q.s.p. 100 cc.

The pH value of this solution is 7.5.

This solution is felt on thehair for 15 minutes at the ambienttemperature. The hair is then rinsed with water and set in aconventional manner.

The hair is easier to arrange, more resilient, and more attractive inappearance.

EXAMPLE II The procedure is the same as in example I, except that thefollowing solution according to the invention is used:

Sodium tetrathionate l5 g. Sodium bicarbonate l g.I-cyclohexyl-3-(2-methylomorpholinium) ethyl carbodiimide] par-toluenelull'onate 5 g. Water q.l.p. I00 cc.

Equally good results are obtained.

EXAMPLE Ill The procedure is the same as in example I, using as thereducing agent in the first step of the permanent waving process:

Thioglycerol 3 g. Ammonia q.s.p. pH Water q.|.p. cc.

Then the permanent is neutralized with the following oxidizing agent:

reducing agent the following solution:

Thiolactic acid 5 g.

Monoethanolamine, q.l.p. pH=9.2

Water q.|.p cc.

The permanent is then neutralized with a composition according to theinvention, consisting of the following solution:

Sodium bromate 7 g. l-ethyl,3-(T-trimethylarnmonium) propylcarbodiimide] paratoluene lulfonate 2 g. Water q.s.p. 100 cc.

The pH value of this solution is 7.5 Equally good results are obtained.

EXAMPLE V The procedure is the same as in example I, using as thereducing agent the following solution:

Ammonium thioglycolate 4 g. Ammonia q.a.p. pH=9.3 Water q.|.p. X00 cc.

and as the composition according to the invention, for neutralizing thepermanent, the following solution:

Sodium tetratluionate l5 g. Sodium bicarbonate l g. [l,l'-bia(3"-trimethylammonium propyl)-3,3'-

hear-ethylene dicarbondiimide] diparatoluene sulfonate 4 g. Water q.s.p.100 cc.

Equally good results are obtained.

ral head of hair, in a conventional manner, by applying as the reducingagent the following composition:

Ammonium thioglycolate g. NlLOi-l qsp. pl l=9.3 Water q.s.p. 100 cc.

The hair is rinsed with hot water, and the oxidizing agent of example11, which has first been warmed, is then applied.

The hair is then covered with a cap until neutralization is complete,that is, for about 15 minutes, and the temperature brought to about 4045C. by heating it under a drier.

Equally good results are obtained.

It will be appreciated that the foregoing examples have been givenpurely by way of illustration, and may be modified as to detail withoutthereby departing from the basic principles of the invention.

We claim:

1. A process for treating hair comprising the steps of first permanentlywaving the hair with a thioreducing agent to rupture the S--S bonds ofthe keratin, and thereafter applying to the hair an aqueous solutionhaving a pH 4-8 and containing 1-20 percent by weight of a neutralizingagent and 0.1- percent by weight of a water soluble diimide compoundselected from the group consisting of:

v and in which R represents a radical selected from the group consistingof lower alkyl having one to six carbon atoms and cyclohexyl R, isselected from the group consistingof:

CH1) nN A" CH R4 and in which R, and R represent a radical selected fromthe group consisting of methyl and ethyl,

n is a whole number 2 to 3 inclusive and A is an ion selected from thegroup consisting of sulfate,

paratoluene sulfonate and iodide, and permitting the solution to remainin contact with the hair for about 5-60 minutes. a

2. The process of claim I wherein the hair is bleached hair and theaqueous solution is left in contact with the hair for about fifteenminutes at ambient temperature.

3. The process of claim 1, wherein the hair is unbleached hair and thesolution is left in contact with the hair for 15-60 minutes.

4. The process of claim 1, wherein the solution contains 2-6 percent ofthe carbodiimide.

5. The process of claim 4, wherein the neutralizing agent is selectedfrom the group consisting of hydrogen peroxide, urea peroxide, alkalimetal bi om ates ang so dium tetrathionate.

2. The process of claim 1 wherein the hair is bleached hair and theaqueous solution is left in contact with the hair for about fifteenminutes at ambient temperature.
 2. R1-N C N-R2 in which R1 represents aradical selected from the group consisting of lower alkyl having one tosix carbon atoms and cyclohexyl R2 is selected from the group consistingof:
 3. The process of claim 1, wherein the hair is unbleached hair andthe solution is left in contact with the hair for 15- 60 minutes.
 4. Theprocess of claim 1, wherein the solution contains 2- 6 percent of thecarbodiimide.
 5. The process of claim 4, wherein the neutralizing agentis selected from the group consisting of hydrogen peroxide, ureaperoxide, alkali metal bromates and sodium tetrathionate.